CN112119513B

CN112119513B - Organic light emitting device

Info

Publication number: CN112119513B
Application number: CN201980032131.9A
Authority: CN
Inventors: 许瀞午; 尹喜敬; 许东旭
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2018-07-24
Filing date: 2019-07-24
Publication date: 2023-12-08
Anticipated expiration: 2039-07-24
Also published as: CN112119513A; KR102209934B1; KR20200011382A; WO2020022771A1

Abstract

The present specification relates to an organic light emitting device, including: a cathode; an anode provided opposite to the cathode; a light-emitting layer provided between the cathode and the anode; a first organic layer which is provided between the cathode and the light-emitting layer and contains a compound of chemical formula 1; and a second organic layer provided between the cathode and the first organic layer and containing a compound of chemical formula 2.

Description

Organic light emitting device

Technical Field

The present specification relates to organic light emitting devices.

The present application claims priority from korean patent application No. 10-2018-0085926, filed to the korean patent office on 24 th 7 of 2018, the entire contents of which are incorporated herein.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light emitting device, the organic layer is formed of a multi-layer structure composed of different substances, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.

There is a continuing need to develop new materials for use in organic light emitting devices as described above.

< Prior Art document > Korean laid-open patent publication No. 10-2007-0091540

Disclosure of Invention

Technical problem

The present specification provides an organic light emitting device.

Solution to the problem

An embodiment of the present specification provides an organic light emitting device, including:

a cathode; an anode provided opposite to the cathode; a light-emitting layer provided between the cathode and the anode; a first organic layer which is provided between the cathode and the light-emitting layer and contains a compound represented by chemical formula 1; and a second organic layer provided between the cathode and the first organic layer and containing a compound represented by chemical formula 2 below.

[ chemical formula 1]

In the above-mentioned chemical formula 1,

x is O or S, and the X is O or S,

at least one of R1 to R16 is a group represented by the following formula A, the others being the same or different from each other, each independently being hydrogen, an alkyl group, or an aryl group substituted or unsubstituted with an alkyl group, or being combined with each other with the adjacent group to form an aromatic hydrocarbon ring,

[ chemical formula A ]

In the above-mentioned chemical formula a,

at least one of X1 to X3 is N, the rest are CR',

R' is hydrogen, or is together with- (L2) _l2 Ar2 or- (L3) _l3 Ar3 is bonded to form an aromatic hydrocarbon ring substituted or unsubstituted with a heterocyclic group,

l1 to L3 are the same or different from each other and are each independently a direct bond; arylene substituted or unsubstituted with alkyl, aryl, or heterocyclyl; or a heterocyclic group having a valence of 2 which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of an alkyl group, an aryl group, a heterocyclic group and an aryl group substituted with an alkyl group,

ar2 and Ar3 are the same or different from each other and are each independently an aryl group substituted or unsubstituted with an alkyl group, a haloalkyl group, a haloalkoxy group, or a heteroaryl group; silyl groups substituted or unsubstituted with alkyl groups or aryl groups; or a heterocyclic group substituted or unsubstituted with an alkyl group, or an aryl group,

l1 to l3 are each independently an integer of 1 to 3,

when L1 is 2 or more, 2 or more L1 s are the same or different from each other,

when L2 is 2 or more, 2 or more L2 s are the same or different from each other,

when L3 is 2 or more, 2 or more L3 s are the same or different from each other,

represents a binding site with the above chemical formula 1,

[ chemical formula 2]

In the above-mentioned chemical formula 2,

at least one of Y1 to Y3 is N, the remainder are CH,

g1 and G2 are the same or different from each other and each independently is an aryl group substituted or unsubstituted with an aryl group,

L11 and L12 are the same or different from each other and each independently is a substituted or unsubstituted aromatic hydrocarbon ring group of 2 to 4 valences or a substituted or unsubstituted heterocyclic group of 2 to 4 valences,

g11 is a direct bond, O, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group having a valence of 2,

a to d are each independently integers of 1 to 3,

when a to d are 2 or more, the structures in parentheses of 2 or more are the same or different from each other.

Effects of the invention

The organic light emitting device according to an embodiment of the present specification has improved electron injection capability from the cathode, so that a low driving voltage and high light emitting efficiency can be provided.

Drawings

Fig. 1 to 5 illustrate examples of an organic light emitting device according to an embodiment of the present specification.

< description of symbols >

101: substrate board

201: anode

301: hole transport layer

401: light-emitting layer

402: a first light-emitting layer

403: a second light-emitting layer

404: third light-emitting layer

501: electron transport layer

601: cathode electrode

701: hole blocking layer

801: hole injection layer

Detailed Description

The present specification will be described in detail below.

A cathode; an anode provided opposite to the cathode; a light-emitting layer provided between the cathode and the anode; a first organic layer which is provided between the cathode and the light-emitting layer and contains a compound represented by chemical formula 1; and a second organic layer provided between the cathode and the first organic layer and containing a compound represented by chemical formula 2.

According to an embodiment of the present specification, the compound of chemical formula 1 is used for a hole blocking layer in a nonlinear structure, so that improvement of efficiency, low driving voltage, life characteristics, and the like of an organic light emitting device can be achieved. In addition, in the structure of the compound represented by the above chemical formula 1, at least one of R1 to R16 is the above chemical formula a, and the above chemical formula a is an electron-depleted structure, so that the polarity (dipole moment) of a molecule can be designed to be nearly nonpolar, so that an amorphous (amorphlus) layer can be formed when an organic light emitting device including the compound represented by the above chemical formula 1 in a hole blocking layer is fabricated. Therefore, the organic light emitting device according to an embodiment of the present specification can achieve an improvement in efficiency, a low driving voltage, an improvement in lifetime characteristics, and the like.

In particular, the compound represented by the above chemical formula 1 has a structure that is stereoscopically horizontal, and thus electron mobility is enhanced when an organic layer is formed using this material.

In this specification, "energy level" refers to the amount of energy. Therefore, the energy level is interpreted as an absolute value representing the energy value. For example, a low or deep energy level means that the absolute value increases from the vacuum level to the negative direction.

In this specification, HOMO (highest occupied molecular orbital ) refers to a molecular orbital function (highest occupied molecular orbital) in which electrons are located in a region with highest energy among regions that can participate in binding, LUMO (lowest unoccupied molecular orbital ) refers to a molecular orbital function (lowest unoccupied molecular orbital) in which electrons are located in a region with lowest energy among anti-bonding regions, and HOMO energy level refers to a distance from a vacuum energy level to HOMO. Further, LUMO level refers to the distance from vacuum level to LUMO.

In the present specification, the band Gap (band Gap) refers to the difference in energy levels of HOMO and LUMO, i.e., HOMO-LUMO Gap (Gap).

According to an embodiment of the present specification, the HOMO level of the compound represented by the above chemical formula 1 may be 6.0eV or more, the triplet (triplet) level may be 2.5eV or more, and the band gap may be 3.0eV or more.

The higher the triplet energy level, the less triplet energy of the light emitting layer is transferred to the adjacent layer, and thus the efficiency of the organic light emitting device can be improved. In addition, in the hole blocking layer, the more the HOMO level has a value of 6.0eV or more, the more the transfer of holes from the light emitting layer can be blocked, and a device with high efficiency and long lifetime can be manufactured.

Thus, when the compound represented by the above chemical formula 1 satisfying the above range is used for a hole blocking layer, the electron mobility is high, and thus characteristics of low driving voltage, high efficiency, and long life are exhibited when used for an organic light emitting device. In addition, the LUMO level has a value of 3.0eV to 2.6eV, and an energy barrier with the light emitting layer is not large, so that electron injection is smoothly performed. The LUMO energy level refers to an energy level of a region having a low energy barrier with the light emitting layer.

In this specification, the HOMO level can be measured at atmospheric pressure by a photoelectron spectrometer (manufactured by Wako Co., ltd.: AC 3), and the LUMO level can be calculated by using a wavelength value measured by photoluminescence (photoluminescence (PL)).

The compound represented by the above chemical formula 2 according to an embodiment of the present specification has a structure in which CN is bonded by a six-membered heterocycle containing N and linking groups L11, G11, and L12, and has a proper twisted structure, and thus electron interactions due to conjugation between substituents become small, whereby independent characteristics of substituents can be maintained, and at the same time, the properly maintained conjugation can prevent a phenomenon of deterioration in the life of an organic light emitting device due to excessive electron injection, and an improvement in efficiency, a low driving voltage, and an improvement in life characteristics can be achieved in the organic light emitting device due to such structural characteristics.

According to an embodiment of the present disclosure, the first organic layer is a hole blocking layer.

According to an embodiment of the present disclosure, the second organic layer is an electron transport layer, an electron injection layer, or an electron injection and transport layer.

According to an embodiment of the present disclosure, the second organic layer is an electron injection layer.

According to an embodiment of the present disclosure, the second organic layer is an electron transport layer.

According to an embodiment of the present disclosure, the second organic layer is an electron injection and transport layer.

According to an embodiment of the present disclosure, the first organic layer is a hole blocking layer, and the hole blocking layer is provided in contact with the light emitting layer.

According to an embodiment of the present disclosure, the first organic layer is a hole blocking layer, the second organic layer is an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the hole blocking layer is provided in contact with the light emitting layer.

According to an embodiment of the present disclosure, when the first organic layer includes the compound represented by the chemical formula 1 and the second organic layer includes the compound represented by the chemical formula 2, since the chemical formula 1 having excellent hole blocking ability and the chemical formula 2 having excellent electron injection and transport ability are simultaneously applied to an organic light emitting device, it is possible to improve driving voltage, efficiency, and/or lifetime characteristics by adjusting substances included in an electron blocking layer and an electron transport layer (or an electron injection and transport layer) and adjusting energy levels between the layers.

In addition, chemical formula 1 of the first organic layer does not include CN, chemical formula 2 of the second organic layer is a structure that must include CN, and the difference in the structure of the compounds included in the first organic layer and the second organic layer is used to adjust the dipole moment and LUMO energy level between the first organic layer and the second organic layer, and to adjust the amount of electrons transferred to the light emitting layer to prevent excessive electrons from being simultaneously injected to the light emitting layer, thereby having an effect of improving the lifetime of the organic light emitting device.

According to an embodiment of the present specification, the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2 satisfy the following chemical formula 1.

[ 1]

|P _El |＞|P _Eb |

In the above-mentioned formula 1

|P _Eb I represents the absolute value of the dipole moment of the compound represented by the above chemical formula 1,

|P _El the "absolute value" represents the absolute value of the dipole moment of the compound represented by the above chemical formula 2.

In the present specification, the dipole moment is a physical quantity indicating the degree of polarity, and can be calculated by the following equation 1.

[ mathematics 1]

·ρ(r ₀ ): molecular Density (molecular density)

V: volume (volume)

R: observation point (the point of observation)

·d ³ r ₀ : per unit volume (an elementary volume)

In the above equation 1, the molecular density is calculated, and a value of the dipole moment can be obtained. For example, the molecular density may be calculated for each atom's Charge (Charge) and Dipole (Dipole) using the herford Charge analysis (Hirshfeld Charge Analysis) method, calculated according to the following equation, and the calculated result may be substituted into the above equation 1 to obtain the Dipole moment.

Weight Function (Weight Function)

·ρ _α (r-R _α ): spherical average ground state density (spherically averaged ground-state amomic density)

·Excimer Density (promolecule density)

Deformation Density (Deformation Density)

ρ (r): molecular Density

·ρ _α (r-R _α ): located at the coordinate R _α Density of free atoms alpha at (density of the free atom alpha located at coordinates R _α )

Atomic Charge (Atomic Charge)

q(α)＝-∫ρd(r)W _α (r)d ³ r

·W _α (r): weighting function

Chemical formula 2 according to an embodiment of the present specification contains a cyano group that does not greatly affect the shape of the entire molecule thereof and can greatly increase the dipole moment, and the structure of chemical formula 1 described above does not contain a cyano group.

Therefore, the dipole moment of chemical formula 2 including the cyano group is greatly increased, and thus the second organic layer including the same and the first organic layer including chemical formula 1 not including the cyano group satisfy the above formula 1, and the dipole moment and LUMO energy level show a large difference, which plays a role of a barrier with the first organic layer in the second organic layer, and adjusts the amount and speed of electrons injected from the cathode to the light emitting layer, thereby having an effect of improving the lifetime of the organic light emitting device.

In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is connected to the other member but also the case where another member exists between the two members.

In the present specification, when a certain component is referred to as "including/comprising" a certain component, unless otherwise specified, it means that other components may be further included, rather than excluded.

In the present specification, examples of the substituents are described below, but are not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" means substituted with 1 or more substituents selected from deuterium, halogen group, hydroxyl group, cyano group, alkyl group, cycloalkyl group, alkenyl group, alkoxy group, aryloxy group, silyl group, halogenoalkyl group, halogenoalkoxy group, aryl group, and heterocyclic group, or substituted with a substituent in which 2 or more substituents among the above exemplified substituents are linked, or does not have any substituent. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethylpropyl, 1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

In the present specification, cycloalkyl is not particularly limited, but cycloalkyl having 3 to 30 carbon atoms is preferable, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like are included, but the present invention is not limited thereto.

In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like are possible, but not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be a single ring or a multiple ring.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specifically, the monocyclic aryl group may be phenyl, biphenyl, terphenyl, or the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specifically, the polycyclic aryl group may be naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, phenalenyl, perylenyl,A group, a fluorenyl group, etc., but is not limited thereto.

In the present specification, the above fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

In the case where the fluorenyl group is substituted, the structure may be as shown below, but is not limited thereto.

In this specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on the atom substituted by the substituent. For example, 2 substituents substituted in the ortho (ortho) position in the benzene ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the heterocyclic group contains 1 or more non-carbon atoms, i.e., hetero atoms, and specifically, the hetero atoms may contain 1 or more atoms selected from O,N, se and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heterocyclic group may be a single ring or a multiple ring. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, pyridoindolyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthridinyl (phenanthrinyl), phenanthroline (phenanthrinyl), iso->Oxazolyl, thiadiazolyl, xanthenyl (xanthone), phenothiazinyl, dibenzofuranyl, dibenzosilol, and pheno ∈>Thioyl (phenoxathiine), pheno +.>Oxazinyl (phenoxazine), phenothiazinyl (phenoxazine), phenazinyl (phenoxazine), dihydroacridinyl, dihydroindenocarbazolyl, and the like, but are not limited thereto.

In the present specification, the aryl group in the aryloxy group is the same as exemplified for the above aryl group. Specifically, examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3, 5-dimethyl-phenoxy group, a 2,4, 6-trimethylphenoxy group, a p-t-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthracenyloxy group, a 2-anthracenyloxy group, a 9-anthracenyloxy group, a 1-phenanthrenyloxy group, a 3-phenanthrenyloxy group, a 9-phenanthrenyloxy group, and the like, but are not limited thereto.

In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.

In the present specification, a haloalkyl group means a group in which hydrogen of an alkyl group is substituted with a halogen group, and examples of the alkyl group other than H which is a halogen group may be applied to the alkyl group. For example, there is-CF ₃ 、-CHF ₂ 、-CH ₂ F, etc., but is not limited thereto.

In the present specification, haloalkoxy means a group in which hydrogen of an alkoxy group is substituted with a halogen group, and among the above alkoxy groups, examples of the above alkoxy groups other than H being a halogen group can be applied. For example, there is-OCF ₃ 、-OCHF ₂ 、-OCH ₂ F, etc., but is not limited thereto.

In the present specification, arylene means a group having two bonding positions on an aryl group, i.e., a 2-valent group. They are each a 2-valent group, and the above description of aryl groups can be applied.

In the present specification, a heterocyclic group having a valence of 2 means a group having two bonding positions on the heterocyclic group, i.e., a valence of 2. In addition to each of them being a 2-valent group, the above description of the heterocyclic group may be applied.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

In the present specification, the aromatic hydrocarbon ring may be a single ring or a plurality of rings, and may be selected from the examples of aryl groups, except for 1.

In this specification, a heterocyclic ring contains 1 or more non-carbon atoms, i.e., hetero atoms, and specifically, the hetero atoms may contain 1 or more atoms selected from O, N, se and S. The heterocyclic ring may be a single ring or multiple rings, may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic and an aliphatic ring, and may be selected from the examples of the heterocyclic groups, except for the 1-valent one.

In the present specification, the aromatic hydrocarbon ring group having 2 to 4 valences may be a single ring or multiple rings, and means a group having 2 to 4 bonding positions on the above aryl group, that is, a 2 to 4 valent group. They may be applied to the above description of aryl groups other than the groups each having a valence of 2 to 4.

In the present specification, a heterocyclic group having 2 to 4 valences may be a single ring or multiple rings, and means that the heterocyclic group has 2 to 4 bonding positions, that is, a 2 to 4-valent group. They may be suitably exemplified by the heterocyclic groups described above, except that each is a 2-to 4-valent group.

According to an embodiment of the present specification, in the above chemical formula 1, X is O.

According to one embodiment of the present specification, in the above chemical formula 1, X is S.

According to an embodiment of the present specification, the above chemical formula 1 is represented by the following chemical formula 1-1 or 1-2.

[ chemical formula 1-1]

[ chemical formulas 1-2]

In the above chemical formulas 1-1 and 1-2,

l1 to L3, L1 to L3, ar2, ar3 and X1 to X3 are as defined in the above formula A,

at least one of X4 to X6 is N, the rest are CR',

r' is hydrogen, or is together with- (L5) _l5 Ar4 or- (L6) _l6 Ar5 is bound toTo form an aromatic hydrocarbon ring substituted or unsubstituted with a heterocyclic group,

l4 to L6 are the same or different from each other and are each independently a direct bond; arylene substituted or unsubstituted with alkyl, aryl, or heterocyclyl; or a heterocyclic group having a valence of 2 which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of an alkyl group, an aryl group, a heterocyclic group and an aryl group substituted with an alkyl group,

Ar4 and Ar5 are the same or different from each other and are each independently an aryl group substituted or unsubstituted with an alkyl group, a haloalkyl group, a haloalkoxy group, or a heteroaryl group; silyl groups substituted or unsubstituted with alkyl groups or aryl groups; or a heterocyclic group substituted or unsubstituted with an alkyl group, or an aryl group,

l4 to l6 are each independently an integer of 1 to 3,

when L4 is 2 or more, 2 or more L4 s are the same or different from each other,

when L5 is 2 or more, 2 or more L5 s are the same or different from each other,

when L6 is 2 or more, 2 or more L6 s are the same or different from each other,

n1 is an integer of 0 to 2,

n2 is an integer of 0 to 2,

1≤n1+n2≤4，

r100 and R101 are the same or different from each other and are each independently hydrogen, alkyl, or aryl substituted or unsubstituted with alkyl, or are combined with each other with the adjacent groups to form an aromatic hydrocarbon ring,

r100 and r101 are each independently integers from 1 to 8,

1≤r100+n1≤8，

1≤r101+n2≤8，

when R100 is 2 or more, 2 or more R100 are the same or different from each other,

when R101 is 2 or more, 2 or more R101 are the same or different from each other.

According to an embodiment of the present specification, in the above chemical formula 1, at least one of R1 to R16 is a group represented by the above chemical formula a, and the others are the same as or different from each other, each being independently hydrogen; an alkyl group; phenyl substituted or unsubstituted with alkyl; a biphenyl group; a terphenyl group; a naphthyl group; triphenylene; or fluorenyl substituted or unsubstituted with an alkyl group, or bonded to each other with an adjacent group to form a benzene ring.

According to an embodiment of the present specification, in the above chemical formula 1, at least one of R1 to R16 is a group represented by the above chemical formula a, and the others are the same as or different from each other, each being independently hydrogen; a methyl group; n-butyl; a tertiary butyl group; phenyl substituted or unsubstituted with methyl, or tert-butyl; a biphenyl group; a terphenyl group; a naphthyl group; triphenylene; or a fluorenyl group substituted or unsubstituted with a methyl group, or a benzene ring is formed by combining adjacent groups with each other.

According to an embodiment of the present specification, 1 or 2 of the above R1 to R16 are the same or different from each other, each is independently a group represented by the above chemical formula a, 0 to 3 of R1 to R16 are alkyl, aryl, or alkylaryl, and the remainder are hydrogen.

According to an embodiment of the present specification, at least one of the above R1 to R16 is a group represented by the following chemical formula a, and the others are the same or different from each other, each independently is hydrogen, alkyl, aryl, or arylalkyl, or is combined with each other with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to an embodiment of the present specification, groups of the above R1 to R16 other than the group represented by the above chemical formula a or groups other than the group that is bonded to an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring are the same or different from each other, and are each independently t-butylphenyl, methyl, t-butyl, phenyl, methylphenyl, n-butyl, naphthyl, triphenylyl, or 9, 9-dimethylfluorenyl.

According to an embodiment of the present specification, among the above-mentioned R1 to R16, groups which can be combined with each other to form an aromatic hydrocarbon ring are R1 and R2, or R15 and R16. That is, according to an embodiment of the present specification, in the above chemical formula 1, at least one of R1 to R16 is a group represented by the above chemical formula a, and the others are the same or different from each other, each is independently hydrogen, alkyl, aryl substituted or unsubstituted with alkyl, or R1 and R2 are combined with each other to form an aromatic hydrocarbon ring, or R15 and R16 are combined with each other to form an aromatic hydrocarbon ring. In this case, the aromatic hydrocarbon ring formed by combining R1 and R2 may be a benzene ring, and the aromatic hydrocarbon ring formed by combining R15 and R16 may be a benzene ring.

According to one embodiment of the present specification, in the chemical formula 1, R1 and R2 are combined with each other to form an aromatic hydrocarbon ring.

According to an embodiment of the present specification, in the above chemical formula 1, R1 and R2 are combined with each other to form a benzene ring.

According to an embodiment of the present specification, in the chemical formula 1, R15 and R16 are combined with each other to form an aromatic hydrocarbon ring.

According to an embodiment of the present specification, in the above chemical formula 1, R15 and R16 are combined with each other to form a benzene ring.

According to an embodiment of the present specification, in the above chemical formula a, L1 to L3 are the same or different from each other, each independently is a direct bond; phenyl substituted or unsubstituted with alkyl, aryl or heterocyclyl; biphenylene substituted or unsubstituted with heterocyclyl; naphthylene, fluorenyl of 2 valency substituted or unsubstituted by alkyl; a 2-valent terphenyl group; a 2-valent pyridyl group substituted or unsubstituted with a heterocyclic group; furyl of valence 2; thienyl of valence 2; dibenzofuranyl of valence 2; dibenzothienyl of valence 2; a carbazolyl group of 2 valency substituted or unsubstituted with an aryl group or an aryl group substituted with an alkyl group; a 2-valent indanocarbazolyl group substituted or unsubstituted with 1 or more substituents selected from alkyl and aryl; a 2-valent benzocarbazolyl group substituted or unsubstituted with an aryl group, or an aryl group substituted with an alkyl group; a 2-valent dibenzosilol group substituted or unsubstituted with an alkyl group; 2-valent phenonesA thienyl group; 2-valent pheno->An oxazinyl group; a phenothiazinyl group having a valence of 2; or a 2-valent phenazinyl group.

According to one embodiment of the present specificationIn the above chemical formula a, L1 to L3 are the same or different from each other, and each is independently a direct bond; phenyl substituted or unsubstituted with methyl, phenyl, pyridyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl; biphenylene substituted or unsubstituted with pyridinyl; a naphthylene group; a 2-valent fluorenyl group substituted or unsubstituted with a methyl group; a 2-valent terphenyl group; a 2-valent pyridyl group substituted or unsubstituted with a pyridyl group; furyl of valence 2; thienyl of valence 2; dibenzofuranyl of valence 2; dibenzothienyl of valence 2; a carbazolyl group of 2 valency substituted or unsubstituted by a phenyl group or a phenyl group substituted by a methyl group; a 2-valent indanocarbazolyl group substituted or unsubstituted with 1 or more substituents selected from methyl and phenyl; a 2-valent benzocarbazolyl group substituted or unsubstituted with a phenyl group or a biphenyl group substituted with a methyl group; a 2-valent dibenzosilol group substituted or unsubstituted with methyl; 2-valent phenones A thienyl group; 2-valent pheno->An oxazinyl group; a phenothiazinyl group having a valence of 2; or a 2-valent phenazinyl group.

According to an embodiment of the present specification, in the above chemical formula a, L1 is a direct bond; phenyl substituted or unsubstituted with alkyl, or aryl; biphenylene; naphthylene, fluorenyl of 2 valency substituted or unsubstituted by alkyl; a 2-valent pyridyl group; furyl of valence 2; thienyl of valence 2; dibenzofuranyl of valence 2; dibenzothienyl of valence 2; a carbazolyl group of 2 valency substituted or unsubstituted with an aryl group or an aryl group substituted with an alkyl group; a 2-valent indanocarbazolyl group substituted or unsubstituted with an alkyl substituent; a 2-valent benzocarbazolyl group substituted or unsubstituted with an aryl group, or an aryl group substituted with an alkyl group; a 2-valent dibenzosilol group substituted or unsubstituted with an alkyl group; 2-valent phenonesA thienyl group; 2-valent pheno->An oxazinyl group; or a phenothiazinyl group having a valence of 2.

According to an embodiment of the present specification, in the above chemical formula a, L1 is a direct bond; phenyl substituted or unsubstituted with methyl, or phenyl; biphenylene; naphthylene, fluorenyl of 2 valency substituted or unsubstituted by methyl; a 2-valent pyridyl group; furyl of valence 2; thienyl of valence 2; dibenzofuranyl of valence 2; dibenzothienyl of valence 2; a carbazolyl group of 2 valency substituted or unsubstituted by a phenyl group or a phenyl group substituted by a methyl group; a 2-valent indanocarbazolyl group substituted or unsubstituted with methyl; a 2-valent benzocarbazolyl group substituted or unsubstituted with a phenyl group or a biphenyl group substituted with a methyl group; a 2-valent dibenzosilol group substituted or unsubstituted with methyl; 2-valent phenones A thienyl group; 2-valent pheno->An oxazinyl group; or a phenothiazinyl group having a valence of 2.

According to an embodiment of the present specification, in the above chemical formula a, L2 and L3 are the same or different from each other, each independently is a direct bond; phenyl substituted or unsubstituted with alkyl, aryl or heterocyclyl; biphenylene substituted or unsubstituted with heterocyclyl; a 2-valent terphenyl group; a 2-valent pyridyl group substituted or unsubstituted with a heterocyclic group; dibenzofuranyl of valence 2; dibenzothienyl of valence 2; a carbazolyl group of 2 valency substituted or unsubstituted with an aryl group; a 2-valent indanocarbazolyl group substituted or unsubstituted with 1 or more substituents selected from alkyl and aryl; or a 2-valent phenazinyl group.

According to an embodiment of the present specification, in the above chemical formula a, L2 and L3 are the same or different from each other, each independently is a direct bond; phenyl substituted or unsubstituted with methyl, phenyl, pyridyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl; biphenylene substituted or unsubstituted with pyridinyl; a 2-valent terphenyl group; a 2-valent pyridyl group substituted or unsubstituted with a pyridyl group; dibenzofuranyl of valence 2; dibenzothienyl of valence 2; a carbazolyl group of valence 2 substituted or unsubstituted by a phenyl group; a 2-valent indanocarbazolyl group substituted or unsubstituted with 1 or more substituents selected from methyl and phenyl; or a 2-valent phenazinyl group.

According to an embodiment of the present specification, in the above chemical formula a, l1 is 1.

According to an embodiment of the present specification, in the above chemical formula a, l1 is 2.

According to an embodiment of the present specification, in the above chemical formula a, l1 is 3.

According to an embodiment of the present specification, in the above chemical formula a, l2 is 1.

According to one embodiment of the present specification, in the above chemical formula a, l2 is 2.

According to one embodiment of the present specification, in the above chemical formula a, l2 is 3.

According to an embodiment of the present specification, in the above chemical formula a, l3 is 1.

According to an embodiment of the present specification, in the above chemical formula a, l3 is 2.

According to one embodiment of the present specification, in the above chemical formula a, l3 is 3.

According to one embodiment of the present specification, in the chemical formula a, when l1 is 2 or more, the l1 is connected in a linear structure. For example, when L1 is a 2-valent carbazolyl group or a phenylene group and L1 is 2 or more, the compound may beThe connection structure is not limited thereto.

According to one embodiment of the present specification, in the chemical formula 1, when l1 is 2 or more, l1 is connected in a linear structure. For example, when L1 is a 2-valent carbazolyl group or a phenylene group and L1 is 3, the compound may be The connection structure is not limited thereto.

According to an embodiment of the present specification, in the above chemical formula a, at least one of X1 to X3 is N, and the rest are CR.

According to an embodiment of the present specification, in the above chemical formula a, X1 is N, and X2 and X3 are CR.

According to an embodiment of the present specification, in the above chemical formula a, X2 is N, and X1 and X3 are CR.

According to an embodiment of the present specification, in the above chemical formula a, X3 is N, and X1 and X2 are CR.

According to an embodiment of the present specification, in the above chemical formula a, X1 and X2 are N, and X3 is CR.

According to an embodiment of the present specification, in the above chemical formula a, X1 and X3 are N, and X2 is CR.

According to an embodiment of the present specification, in the above chemical formula a, X2 and X3 are N, and X1 is CR.

According to an embodiment of the present specification, in the above chemical formula a, X1 to X3 are N.

According to one embodiment of the present specification, R is hydrogen or- (L2) _l2 Ar2 or- (L3) _l3 Ar3 combines to form a phenyl ring substituted or unsubstituted with a heterocyclic group.

According to one embodiment of the present specification, R is hydrogen or- (L2) _l2 Ar2 or- (L3) _l3 Ar3 is combined to form a benzene ring substituted or unsubstituted by a benzocarbazolyl group.

According to an embodiment of the present specification, in the above chemical formula a, ar2 and Ar3 are the same or different from each other, each independently is a silyl group substituted or unsubstituted with an alkyl group or an aryl group; phenyl substituted or unsubstituted with alkyl or haloalkyl; biphenyl substituted or unsubstituted with haloalkyl; a naphthyl group; terphenyl substituted or unsubstituted with haloalkyl, haloalkoxy, or heterocyclyl; fluorenyl substituted or unsubstituted with alkyl; phenanthryl; triphenylene; a fluoranthenyl group; a phenyl group; a pyridyl group; dibenzofuranyl substituted or unsubstituted with alkyl; dibenzothienyl; carbazolyl substituted or unsubstituted with alkyl, or aryl; a benzocarbazolyl group; substituted or unsubstituted by alkyl groupsSubstituted dibenzosilol; phenonesAn oxazinyl group; a phenothiazinyl group; pheno->A thienyl group; pyridoindolyl; quinolinyl; an alkyl-substituted or unsubstituted indanocarbazolyl group; or a dihydroacridinyl group substituted or unsubstituted with an alkyl group.

According to an embodiment of the present specification, in the above chemical formula a, ar2 and Ar3 are the same or different from each other, each independently is a silyl group substituted or unsubstituted with a methyl group or a phenyl group; by methyl groups, or-CF ₃ A substituted or unsubstituted phenyl group; is-CF ₃ Substituted or unsubstituted biphenyl; a naphthyl group; is-CF ₃ 、-OCF ₃ Or pyridyl substituted or unsubstituted terphenyl; fluorenyl substituted or unsubstituted with methyl; phenanthryl; triphenylene; a fluoranthenyl group; a phenyl group; a pyridyl group; dibenzofuranyl substituted or unsubstituted with methyl; dibenzothienyl; carbazolyl substituted or unsubstituted with methyl, phenyl, or biphenyl; a benzocarbazolyl group; a dibenzosilol group substituted or unsubstituted with a methyl group; phenonesAn oxazinyl group; a phenothiazinyl group; pheno->A thienyl group; pyridoindolyl; quinolinyl; a indanocarbazolyl group substituted or unsubstituted with methyl; or a dihydroacridinyl group substituted or unsubstituted with a methyl group.

According to an embodiment of the present specification, the above chemical formula a is represented by any one of the following chemical formulas a-1 to a-3.

[ formula A-1]

[ formula A-2]

[ formula A-3]

In the above formulas a-1 to a-3,

l1 and L1 are as defined in formula A,

x11 is N or CH, X12 is N or CH, X13 is N or CH, at least 2 of X11 to X13 are N,

ar21 to Ar24 are the same as or different from each other and are each independently an aryl group substituted with 1 substituent selected from the group consisting of "cyano group, halogen group, alkyl group, alkoxy group, aryl group, trialkylsilyl group, triarylsilyl group and heterocyclic group", or a substituent formed by joining 2 groups selected from the above group, or a substituent formed by joining 3 groups selected from the above group; silyl groups substituted or unsubstituted with alkyl or aryl groups; or a heterocyclic group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of "alkyl group, aryl group, alkylaryl group, heteroaryl group and heterocyclic group",

R50 and R51 are identical or different from each other and are each independently hydrogen, alkyl, aryl or heteroaryl,

a50 is an integer of 0 to 4, R50 are the same or different from each other when a50 is 2 or more,

a51 is an integer of 0 to 4, and when a51 is 2 or more, R51 are the same or different from each other.

According to an embodiment of the present specification, the L1 position is directly bonded; arylene substituted or unsubstituted with alkyl, aryl, or heterocyclyl; or a heterocyclic group of 2 valency substituted or unsubstituted by an alkyl group, an alkylaryl group or an aryl group.

According to an embodiment of the present disclosure, L1 is a direct bond; c6-18 arylene substituted or unsubstituted with C1-6 alkyl, C6-20 aryl, or C2-20 heteroaryl; or a C2-20 heterocyclic group having a valence of 2 which is substituted or unsubstituted by a C1-6 alkyl group, a C6-20 alkylaryl group or a C6-20 aryl group.

According to an embodiment of the present disclosure, L1 is a direct bond; c6-13 arylene substituted or unsubstituted with C1-6 alkyl, C6-12 aryl, or C2-12 heteroaryl; or a C2-16 heterocyclic group of 2 valence which is substituted or unsubstituted by a C1-6 alkyl group, a C6-16 alkylaryl group or a C6-15 aryl group.

According to an embodiment of the present specification, L1 is a directly bonded, methyl-or phenyl-substituted or unsubstituted phenylene group, biphenylene group, 2-valent naphthyl group, 2-valent furyl group, 2-valent thienyl group, 2-valent pyridyl group, 2-valent dibenzofuranyl group, 2-valent dibenzothienyl group, methyl-or phenyl-substituted or unsubstituted 2-valent carbazolyl group, methyl-substituted biphenyl-or phenyl-substituted or unsubstituted 2-valent benzocarbazolyl group, methyl-substituted or unsubstituted 2-valent indenocarbazolyl group, methyl-substituted or unsubstituted 2-valent dibenzosilol group, Or a 2-valent fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group.

According to an embodiment of the present specification, the above Ar21 to Ar24 are the same as or different from each other, each independently being a trialkylsilyl group; a triarylsilyl group; aryl substituted or unsubstituted with 1 or more substituents selected from cyano, haloalkyl, haloalkoxy, trialkylsilyl, triarylsilyl, alkyl, aryl, and heterocyclyl substituted or unsubstituted with "alkyl, alkylaryl, aryl, or heterocyclyl"; or a heterocyclic group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of an alkyl group, a heteroaryl group, an aryl group and a heterocyclic group.

According to an embodiment of the present specification, the above Ar21 to Ar24 are the same as or different from each other, each independently being a triphenylsilyl group; phenyl optionally substituted by trifluoromethyl, trifluoromethoxy, trimethylsilyl, methyl, biphenyl, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, phenyl or pyridinyl, indenocarbazolyl, dimethyldibenzosilol or quinolinyl; biphenyl substituted or unsubstituted with cyano, haloalkyl, trimethylsilyl, triphenylsilyl, pyridyl or carbazolyl; naphthyl substituted or unsubstituted by phenyl; a benzocarbazolyl group; dibenzofuranyl; dibenzothienyl; carbazolyl substituted or unsubstituted with carbazolylphenyl or phenyl; terphenyl substituted or unsubstituted with pyridinyl; fluorenyl substituted or unsubstituted with methyl or phenyl; a phenyl group; phenanthryl; or triphenylene, or any one selected from the following structures.

According to an embodiment of the present specification, the above R50 and R51 are the same or different from each other, and each is independently heteroaryl.

According to an embodiment of the present specification, R50 and R51 are the same or different from each other, and each is independently a benzocarbazolyl group.

According to an embodiment of the present specification, the compound represented by the above chemical formula 1 is selected from the following compounds.

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According to an embodiment of the present specification, in the above chemical formula 2, a is 1.

According to an embodiment of the present specification, in the above chemical formula 2, a is 2.

According to an embodiment of the present specification, in the above chemical formula 2, a is 3.

According to an embodiment of the present specification, the above chemical formula 2 is represented by any one of the following chemical formulas 2-1 to 2-3.

[ chemical formula 2-1]

[ chemical formula 2-2]

[ chemical formulas 2-3]

In the above chemical formulas 2-1 to 2-3,

y1 to Y3, G1, G2, L11, L12, G11, b and d are as defined in the above chemical formula 2,

at least one of Y4 to Y6 is N, the balance is CH, at least one of Y7 to Y9 is N, the balance is CH,

g3 to G6 are the same as or different from each other and each independently is an aryl group substituted or unsubstituted with an aryl group.

According to an embodiment of the present specification, in the above chemical formula 2, Y1 is N, and Y2 and Y3 are CH.

According to an embodiment of the present specification, in the above chemical formula 2, Y2 is N, and Y1 and Y3 are CH.

According to an embodiment of the present specification, in the above chemical formula 2, Y3 is N, and Y1 and Y2 are CH.

According to an embodiment of the present specification, in the above chemical formula 2, Y1 and Y2 are N, and Y3 is CH.

According to an embodiment of the present specification, in the chemical formula 2, Y1 and Y3 are N, and Y2 is CH.

According to an embodiment of the present specification, in the above chemical formula 2, Y2 and Y3 are N, and Y1 is CH.

According to an embodiment of the present specification, in the above chemical formula 2, Y1 to Y3 are N.

According to an embodiment of the present specification, in the above chemical formula 2, G1 and G2 are the same or different from each other, and each is independently a phenyl group, a biphenyl group, or a fluorenyl group substituted or unsubstituted with an aryl group.

According to an embodiment of the present specification, in the above chemical formula 2, G1 and G2 are the same or different from each other, and each is independently a phenyl group, a biphenyl group, or a fluorenyl group substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, each of the above-mentioned G1 and G2, which are the same or different from each other, is independently a phenyl group, a biphenyl group, or a 9, 9-diphenyl-9H-fluorenyl group.

According to an embodiment of the present specification, in the above chemical formula 2, L11 and L12 are the same or different from each other, and each is independently an aromatic hydrocarbon ring group of 2 to 4 valences substituted or unsubstituted with cyano, aryl, heterocyclic group, aryl substituted with cyano and alkyl, aryl substituted with heterocyclic group, or aryl substituted with cyano; or a heterocyclic group having a valence of 2 to 4.

According to an embodiment of the present specification, in the above chemical formula 2, L11 and L12 are the same or different from each other, and each is independently a phenyl group of 2 to 4 valences substituted or unsubstituted with cyano, aryl, heterocyclic group, aryl substituted with cyano and alkyl, aryl substituted with heterocyclic group, or aryl substituted with cyano; a biphenyl group of 2 to 4 valences substituted or unsubstituted with an aryl group substituted with a cyano group; naphthyl of 2 to 4 valences; a terphenyl group of 2 to 4 valences substituted or unsubstituted with an aryl group substituted with a cyano group; fluorenyl of 2 to 4 valences substituted or unsubstituted with alkyl; or a xanthenyl group of 2 to 4 valencies.

According to an embodiment of the present specification, in the above chemical formula 2, L11 and L12 are the same or different from each other, and each is independently a phenyl group having 2 to 4 valences substituted with a cyano group, a biphenyl group, a phenanthryl group, a dibenzothienyl group, a xanthenyl group, a fluorenyl group substituted with a phenyl group, a fluorenyl group substituted with a cyano group and a methyl group, a phenyl group substituted with a pyridyl group, or a phenyl group substituted or unsubstituted with a cyano group; a biphenyl group of 2 to 4 valences substituted or unsubstituted with a phenyl group substituted with a cyano group; naphthyl of 2 to 4 valences; a terphenyl group of 2 to 4 valences substituted or unsubstituted with a phenyl group substituted with a cyano group; a fluorenyl group of 2 to 4 valence substituted or unsubstituted with a methyl group; or a xanthenyl group of 2 to 4 valencies.

According to an embodiment of the present specification, L11 is an aromatic hydrocarbon ring group having 2 to 4 carbon atoms and having 6 to 17 carbon atoms, which is substituted or unsubstituted with R21, or a heterocyclic group having 2 to 30 carbon atoms and having 2 to 4 carbon atoms and having 2 to 30 carbon atoms, which is substituted or unsubstituted with R21.

According to an embodiment of the present specification, L11 is an aromatic hydrocarbon ring group having 2 to 4 carbon atoms and having 6 to 13 carbon atoms, which is substituted or unsubstituted with R21, or a heterocyclic group having 2 to 25 carbon atoms and having 2 to 4 carbon atoms and having 2 to 25 carbon atoms, which is substituted or unsubstituted with R21.

According to an embodiment of the present specification, L11 is an aryl group having 2 to 4 carbon atoms having 6 to 13 which is substituted or unsubstituted with R21, or a heterocyclic group having 2 to 4 carbon atoms having 2 to 25 which is substituted or unsubstituted with R21 and contains only O as a hetero atom.

According to an embodiment of the present specification, L11 is a substituted or unsubstituted phenyl group having a valence of 2 to 4, a substituted or unsubstituted naphthyl group having a valence of 2 to 4, a substituted or unsubstituted fluorenyl group having a valence of 2 to 4, or a substituted or unsubstituted spiro [ fluorene-9, 9' ] xanthenyl group having a valence of 2 to 4.

According to an embodiment of the present specification, L11 is a phenyl group having a valence of 2 to 4, a naphthyl group having a valence of 2 or 4, which is substituted or unsubstituted by R21, a fluorenyl group having a valence of 2 to 4, which is substituted or unsubstituted by methyl or phenyl, or a spiro [ fluorene-9, 9' -xanthene ] group having a valence of 2 to 4.

According to an embodiment of the present specification, R21 is aryl substituted or unsubstituted with cyano, alkyl, aryl or heteroaryl; or a heterocyclic group.

According to an embodiment of the present specification, R21 is aryl substituted or unsubstituted with cyano, alkyl, aryl or N-containing heteroaryl; or an O-containing heterocyclic group.

According to an embodiment of the present specification, the above R21 is 9, 9-dimethyl-9H-fluorenyl substituted or unsubstituted with cyano, spiro [ fluorene-9, 9' -xanthenyl ] group, or phenyl substituted with pyridyl.

In one embodiment of the present specification, L12 is an aromatic hydrocarbon ring group of 2 valences substituted or unsubstituted with R22, or a heterocyclic group of 2 valences substituted or unsubstituted with R23.

In one embodiment of the present specification, L12 is an aromatic hydrocarbon ring group of 2 valences or a heterocyclic group of 2 valences, which is substituted or unsubstituted with R22.

In one embodiment of the present specification, L12 is an aromatic hydrocarbon ring group having 2 valences of 6 to 20 or a heterocyclic group having 2 to 30 carbon atoms, which is substituted or unsubstituted with R22.

In one embodiment of the present specification, L12 is an aromatic hydrocarbon ring group having 2 valences of 6 to 15 or a heterocyclic group having 2 to 25 carbon atoms, which is substituted or unsubstituted with R22.

In one embodiment of the present specification, R22 is aryl or heteroaryl substituted or unsubstituted with cyano or heteroaryl.

In one embodiment of the present specification, R22 is an aryl group substituted or unsubstituted with cyano or N-containing heteroaryl, or a heteroaryl group containing O or S.

In one embodiment of the present specification, R22 is an aryl group substituted or unsubstituted with cyano or heteroaryl containing only N as a heteroatom, or heteroaryl containing only O or S as a heteroatom.

In one embodiment of the present specification, R22 is dibenzothienyl, phenanthryl, cyanophenyl, or pyridylphenyl.

In one embodiment of the present specification, L21 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted fluorenyl group of 2 valency, a substituted or unsubstituted naphthyl group of 2 valency, or a substituted or unsubstituted spiro [ fluorene-9, 9' -xanthenyl ] group of 2 valency.

In one embodiment of the present specification, the above L21 is phenylene substituted or unsubstituted with dibenzothienyl, phenanthryl, cyanophenyl, or pyridylphenyl; 9, 9-dimethyl-9H-fluorenyl of valence 2; 9, 9-diphenyl-9H-fluorenyl of valence 2; naphthyl of valence 2; or a spiro [ fluorene-9, 9' -xanthene ] group of valence 2.

According to an embodiment of the present specification, in the above chemical formula 2, G11 is a direct bond; o; an aryl group substituted or unsubstituted with an alkyl group or with a cyano group; or a heterocyclic group having a valence of 2.

According to an embodiment of the present specification, in the above chemical formula 2, G11 is a direct bond; o; a phenylene group; a naphthylene group; fluorenyl of 2 valency substituted or unsubstituted by alkyl, cyanoaryl or aryl; dibenzofuranyl of valence 2; or a spiro [ fluorene-9, 9' -xanthene ] group of valence 2.

According to an embodiment of the present specification, in the above chemical formula 2, G11 is a direct bond; o; a phenylene group; a naphthylene group; fluorenyl substituted or unsubstituted with methyl, cyanophenyl, or phenyl, having a valence of 2; dibenzofuranyl of valence 2; or a spiro [ fluorene-9, 9' -xanthene ] group of valence 2.

According to one embodiment of the present disclosure, G11 is a direct bond; -O-; arylene substituted or unsubstituted with alkyl, aryl, or cyanoaryl; or contains an O heteroarylene group.

According to an embodiment of the present specification, G11 is a directly bonded, cyano-aryl-substituted or unsubstituted phenylene group, a 2-valent naphthyl group, an alkyl-or aryl-substituted or unsubstituted 2-valent fluorenyl group, a 2-valent dibenzofuranyl group, -O-, or a 2-valent spiro [ fluorene-9, 9' -xanthene ] group.

According to an embodiment of the present specification, G11 is a directly bonded, cyano-phenyl-substituted or unsubstituted phenylene group, a 2-valent naphthyl group, a 2-valent fluorenyl group substituted or unsubstituted by methyl or phenyl group, a 2-valent dibenzofuranyl group, -O-, or a 2-valent spiro [ fluorene-9, 9' -xanthene ] group.

According to an embodiment of the present description, b is 1 or 2.

According to an embodiment of the present specification, in the above chemical formula 2, c is 1.

According to an embodiment of the present specification, in the above chemical formula 2, c is 2.

According to an embodiment of the present specification, in the above chemical formula 2, c is 3.

According to an embodiment of the present specification, in the above chemical formula 2, d is 1.

According to an embodiment of the present specification, in the above chemical formula 2, d is 2.

According to an embodiment of the present specification, in the above chemical formula 2, d is 3.

According to one embodiment of the present specification, in the chemical formula 2, when d is 2 or more, the G11 is connected in a linear structure. For example, when G11 is phenylene or naphthylene and d is 2, it may beAnd the connection structure is not limited thereto.

According to an embodiment of the present specification, the compound represented by the above chemical formula 2 is selected from the following compounds.

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According to an embodiment of the present disclosure, the light emitting layer includes a host and a dopant, and the dopant has a maximum light emitting wavelength in a range of 420nm to 520 nm.

According to an embodiment of the present disclosure, the dopant is a blue fluorescent dopant.

In this specification, an organic light emitting device including a first organic layer including a compound represented by the above chemical formula 1 between a cathode and a light emitting layer and including a second organic layer including a compound represented by the above chemical formula 2 between the above cathode and the first organic layer has an effect of improving the lifetime of the organic light emitting device emitting blue light as a blue organic light emitting device.

According to an embodiment of the present disclosure, the body may include 1 or more materials.

According to an embodiment of the present specification, the above-described body includes at least one of the compounds represented by the following chemical formulas 3-1 and 3-2. When the compound described below is contained, the energy levels of the organic layer and the light-emitting layer are appropriately formed, so that the amount of electrons migrating from the organic layer to the light-emitting layer can be easily adjusted, and thus, the life of the organic light-emitting device can be improved.

[ chemical formula 3-1]

[ chemical formula 3-2]

In the above chemical formulas 3-1 and 3-2,

l31 to L35 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group having a valence of 2,

ar31 to Ar35 are the same as or different from each other, each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

r200 and R201 are the same or different from each other and are each independently hydrogen, or a substituted or unsubstituted aryl group,

r200 is an integer of 1 to 8,

r201 is an integer of 1 to 7,

when R200 is 2 or more, 2 or more R200 are the same or different from each other,

when R201 is 2 or more, 2 or more R201 are the same or different from each other.

According to an embodiment of the present specification, the above-mentioned L31 to L35 are the same or different from each other, and each is independently a direct bond, or an arylene group.

According to an embodiment of the present specification, the above-mentioned L31 to L35 are the same or different from each other, and each is independently a direct bond, a phenylene group, a naphthylene group, or a 2-valent fluoranthene group.

According to an embodiment of the present specification, the above-mentioned Ar31 to Ar35 are the same as or different from each other, and each is independently an aryl group substituted or unsubstituted with deuterium, or a heterocyclic group substituted or unsubstituted with aryl.

According to an embodiment of the present specification, the above Ar31 to Ar35 are the same as or different from each other, and each is independently a phenyl group substituted or unsubstituted with deuterium, a biphenyl group, a naphthyl group, a thienyl group substituted or unsubstituted with phenyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzo [ b ] naphtho [1,2-d ] furyl group, a benzo [ b ] naphtho [2,3-d ] furyl group, or a benzo [ d ] naphtho [1,2-b ] furyl group.

According to an embodiment of the present specification, R200 is hydrogen or aryl substituted or unsubstituted.

According to an embodiment of the present specification, R200 is hydrogen or naphthyl substituted or unsubstituted with phenyl.

According to an embodiment of the present disclosure, R201 is hydrogen.

According to an embodiment of the present specification, the main body is any one or more selected from the following compounds.

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According to an embodiment of the present specification, the compounds of the above chemical formulas 1 and 2 may be manufactured using starting materials, reaction conditions known in the art. The kind and number of substituents can be determined by appropriately selecting known starting materials by those skilled in the art. Further, the compounds of the above chemical formulas 1 and 2 can be obtained from commercially available compounds.

In an embodiment of the present specification, the organic light emitting device may include 2 or more light emitting layers. The above 2 or more light-emitting layers may be provided in contact with each other, or may be provided by including another organic layer between two light-emitting layers.

In one embodiment of the present disclosure, the organic light emitting device may include 2 or more light emitting layers, a charge generating layer may be included between adjacent 2 light emitting layers in the light emission of the 2 or more light emitting layers, and the charge generating layer may include an n-type organic layer and a p-type organic layer.

In another embodiment, the n-type organic layer included in the charge generation layer is NP-bonded to the p-type organic layer.

In one embodiment of the present disclosure, the p-type organic layer is selected from a hole injection layer, a hole transport layer, an electron blocking layer, and a light emitting layer, and the n-type organic layer is selected from an electron transport layer, an electron injection layer, a hole blocking layer, and a light emitting layer.

In this specification, n-type refers to n-type semiconductor characteristics. In other words, the n-type refers to a characteristic of injecting or transporting electrons through a LUMO (lowest unoccupied molecular orbital) energy level, which may be defined as a characteristic of a substance having mobility of electrons larger than mobility of holes. Conversely, p-type refers to p-type semiconductor characteristics. In other words, p-type refers to a property of injecting or transporting holes by HOMO (highest occupied molecular orbital) energy level, which can be defined as a property of a substance having a mobility of holes larger than that of electrons. In this specification, a compound or organic layer having n-type characteristics may be referred to as an n-type compound or n-type organic layer. In addition, the compound or organic layer having p-type characteristics may be referred to as a p-type compound or p-type organic layer. In addition, n-type doping may refer to doping to have n-type characteristics.

In this specification, the charge generation layer refers to a layer that generates charges without applying an external voltage, and charges are generated between adjacent light emitting layers among the 2 or more light emitting layers, so that the 2 or more light emitting layers included in the organic light emitting device can emit light.

In the present specification, the NP bonding means not only that the second electron transport layer as an n-type organic layer is physically connected to a p-type organic layer, but also that the generation and transport of holes and electrons can easily be performed.

According to an embodiment of the present specification, holes or electrons can be easily formed by an external power source or a light source when NP bonding is formed. Therefore, the rise of the driving voltage for hole injection can be prevented.

In another embodiment, the maximum emission wavelengths of at least 2 layers among the above-mentioned 2 or more light-emitting layers are the same or different from each other.

In the present specification, the maximum emission wavelength refers to a wavelength at the maximum of the spectral distribution.

In one embodiment of the present specification, the maximum emission wavelengths of at least 2 layers among the above-mentioned 2 or more light-emitting layers are different from each other.

In one embodiment of the present disclosure, at least one of the 2 or more light-emitting layers contains a phosphorescent dopant, and at least one of the 2 or more light-emitting layers contains a fluorescent dopant.

As in the embodiment of the present specification, a light-emitting layer including 2 or more layers different from each other can be manufactured, and a stack of blue fluorescence, green phosphorescence, and red phosphorescence can be used; a device that emits white light by stacking blue fluorescence and yellow-green phosphorescence. Specifically, an organic light emitting device according to an embodiment of the present specification may include a fluorescent light emitting layer and/or a phosphorescent light emitting layer.

For example, the peak wavelength of the photoluminescence spectrum is 400nm to 500nm for blue, 510nm to 580nm for green, and 610nm to 680nm for red, so that one skilled in the art can combine 1 or 2 or more light emitting layers having different peak wavelengths from each other as needed.

In the present specification, the phosphorescent dopant and the fluorescent dopant may be used as dopants generally used in the art.

In an embodiment of the present specification, the organic light emitting device includes: a first light-emitting layer provided between the anode and the first organic layer, and a second light-emitting layer provided on the first light-emitting layer.

In this case, the first light-emitting layer and the second light-emitting layer may be provided in contact with each other, and a separate organic layer may be provided between the first light-emitting layer and the second light-emitting layer.

In another embodiment of the present specification, the above organic light emitting device includes: a first light-emitting layer provided between the anode and the first organic layer, and a second light-emitting layer provided between the anode and the first organic layer and the remaining part of the first light-emitting layer. An insulating structure may be included between the first light emitting layer and the second light emitting layer.

In this case, the first light-emitting layer and the second light-emitting layer may be provided side by side on the same surface as the first organic layer. In another embodiment, one side surface of the first light emitting layer and one side surface of the second light emitting layer may be in contact with each other.

In one embodiment of the present specification, the first light-emitting layer and the second light-emitting layer provided in parallel may be provided in contact with each other on the same surface of the first organic layer.

In another embodiment, a separate layer may be provided between the first light-emitting layer and the second light-emitting layer, which are provided in parallel, and the first organic layer.

According to an embodiment of the present specification, the above organic light emitting device includes: a first light-emitting layer provided between the anode and the first organic layer, a second light-emitting layer provided on the first light-emitting layer, and a third light-emitting layer provided on the second light-emitting layer.

In this case, the first light-emitting layer, the second light-emitting layer, and the third light-emitting layer may be provided in contact with each other, and another organic layer may be provided between the first light-emitting layer and the second light-emitting layer and/or between the second light-emitting layer and the third light-emitting layer.

In another embodiment, the first light emitting layer, the second light emitting layer, and the third light emitting layer have different maximum light emission wavelengths from each other.

In another embodiment, the first light emitting layer, the second light emitting layer, and the third light emitting layer have the same maximum emission wavelength.

In another embodiment, the first, second, and third light emitting layers may include blue fluorescent dopants, and the maximum light emitting wavelength of the dopants may be in a range of 420nm to 520 nm.

For example, the structure of the organic light emitting device according to the present invention may have the structure shown in fig. 1 to 5, but is not limited thereto.

Fig. 1 illustrates a structure of an organic light emitting device in which an anode 201, a hole transport layer 301, a light emitting layer 401, a hole blocking layer 701, an electron transport layer 501, and a cathode 601 are sequentially stacked on a substrate 101. In fig. 1, the hole blocking layer 701 may be a first organic layer, and the electron transport layer 501 may be a second organic layer. The anode 201 and the hole transport layer 301 may further include a hole injection layer therebetween, and the hole injection layer may be further provided as shown in fig. 2. Fig. 2 illustrates a structure of an organic light-emitting device in which an anode 201, a hole injection layer 801, a hole transport layer 301, a light-emitting layer 401, a hole blocking layer 701, an electron transport layer 501, and a cathode 601 are sequentially stacked on a substrate 101. In fig. 2, the hole blocking layer 701 is a first organic layer, and the electron transport layer 501 may be a second organic layer. In one embodiment, in fig. 2 described above, an electron injection and transport layer may be introduced instead of the electron transport layer 501. The electron injection and transport layer refers to a layer in which electron injection and transport are performed simultaneously, and as a material of the electron injection and transport layer, a material of the electron injection layer and/or the electron transport layer may be used.

Fig. 3 illustrates a structure of an organic light emitting device in which an anode 201, a hole transport layer 301, a first light emitting layer 402, a second light emitting layer 403, a hole blocking layer 701, an electron transport layer 501, and a cathode 601 are sequentially stacked on a substrate 101. In fig. 3, the hole blocking layer 701 may be a first organic layer, the electron transport layer 501 may be a second organic layer, and the first light emitting layer 402 and the second light emitting layer 403 may be provided in contact with each other, and may be provided with another organic layer.

Fig. 4 illustrates a structure of an organic light-emitting device in which an anode 201 and a hole transport layer 301 are provided on a substrate 101, a first light-emitting layer 402 and a second light-emitting layer 403 are provided on the hole transport layer 301, and a hole blocking layer 701, an electron transport layer 501, and a cathode 601 are sequentially stacked on the first light-emitting layer 402 and the second light-emitting layer 403. In fig. 4, the hole blocking layer 701 may be a first organic layer, and the electron transport layer 501 may be a second organic layer.

Fig. 5 illustrates a structure of an organic light emitting device in which an anode 201, a hole transporting layer 301, a first light emitting layer 402, a second light emitting layer 403, a third light emitting layer 404, a hole blocking layer 701, an electron transporting layer 501, and a cathode 601 are sequentially stacked on a substrate 101. In fig. 5, the hole blocking layer 701 may be a first organic layer, the electron transport layer 501 may be the second organic layer, the first light emitting layer 402, the second light emitting layer 403, and the third light emitting layer 404 may be in contact with each other, and another organic layer may be provided between the first light emitting layer 402 and the second light emitting layer 403 and/or between the second light emitting layer 403 and the third light emitting layer 404.

Fig. 1 to 5 are exemplary structures according to embodiments of the present specification, and may further include other organic layers. In addition, in fig. 1 to 5, the first organic layer may be an electron injection layer, or an electron injection and transport layer, instead of the electron transport layer 501.

The organic light emitting device of the present specification may be manufactured by a method known in the art, except that the organic light emitting device includes a first organic layer including the compound represented by the chemical formula 1 between the cathode and the light emitting layer and includes a second organic layer represented by the chemical formula 2 between the cathode and the first organic layer. For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. At this time, it can be manufactured as follows: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by PVD (physical vapor deposition) method such as sputtering (sputtering) or electron beam evaporation (physical Vapor Deposition), then an organic layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, and an electron injection layer is formed on the anode, and then a substance that can function as a cathode is vapor deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. In addition to these methods, an anode material, an organic layer, and a cathode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.

The organic layer of the organic light-emitting device of the present specification may be constituted by a multilayer structure in which 1 or more organic layers are stacked.

In an embodiment of the present specification, the organic light emitting device may further include 1 layer or 2 layers or more selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

As the anode materialIn general, a substance having a large work function is preferable in order to smoothly inject holes into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO ₂ A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.

As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO ₂ And/or Al, but is not limited thereto.

The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers.

The electron blocking layer is a layer that prevents electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer, and thus can improve the lifetime and efficiency of the device, and if necessary, a suitable portion between the light emitting layer and the hole injection layer can be formed using a known material.

The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and a hole-transporting substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer is preferable, and a substance having a large mobility to the holes is preferable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.

When the organic light-emitting device further includes a light-emitting layer other than the light-emitting layer according to an embodiment of the present specification, the light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As a specific example, there is 8-hydroxyquinoline aluminum complex (Alq ₃ ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto.

In the above-mentioned fluorescent light-emitting layer, 1 or more selected from the group consisting of Distyrylarylene (DSA), distyrylarylene derivatives, distyrylbenzene (DSB), distyrylbenzene derivatives, DPVBi (4, 4'-bis (2, 2' -biphenylvinyl) -1,1'-biphenyl, 4' -bis (2, 2'-diphenyl vinyl) -1,1' -biphenyl), DPVBi derivatives, spiro-DPVBi and spiro-6P (spiro-hexabiphenyl).

In the above-mentioned fluorescent light-emitting layer, 1 or 2 or more of dopant substances are selected from the group consisting of styrylamine (styrylamine) system, perylene (perylene) system and DSBP (distyrylbiphenyl) system.

The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. In the case where the organic light emitting device includes an electron injection layer other than the electron injection layer containing the compound represented by the above chemical formula 2, specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, a,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.

Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and when the organic light emitting device includes another electron transporting layer other than the electron transporting layer including the compound represented by the chemical formula 2, the electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light emitting layer, and a substance having a large mobility to electrons is suitable. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq ₃ But not limited to, complexes of (c) and (d), organic radical compounds, hydroxy brass-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed generally under the same conditions as those of the hole injection layer. When the organic light emitting device includes an additional hole blocking layer other than the hole blocking layer including the compound represented by the above chemical formula 1, specific hole blocking substances include The diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.

The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.

In addition, the organic light emitting device according to the present specification may have a positive structure (normal type) in which the lower electrode is an anode and the upper electrode is a cathode, or may have a reverse structure (inverted type) in which the lower electrode is a cathode and the upper electrode is an anode.

The structure according to an embodiment of the present specification can also function in an organic electronic device typified by an organic solar cell, an organic photoreceptor, an organic transistor, or the like, on a principle similar to that applied to an organic light-emitting device.

Modes for carrying out the invention

In the following, examples are given to explain the present specification in detail. However, the embodiments according to the present specification may be modified into various forms, and the scope of the present specification is not to be construed as limited to the embodiments described in detail below. The embodiments of the present description are provided to more fully explain the present description to those skilled in the art.

< Synthesis of Compound of chemical formula 1 >

A method for synthesizing a compound represented by chemical formula 1 according to an embodiment of the present invention will be described by taking a method for synthesizing a compound 1-1 as an example.

[ Synthesis of Compound 1-1 ]

9H-fluoren-9-one (6.95 g,38.6 mmol) and 4-bromophenol (13.35 g,77.2 mmol) were combined with excess phosphorus oxychloride (POCl) ₃ ) The mixture was refluxed at 120 ℃. After cooling to room temperature, an excessive amount of ethanol was added, followed by filtration. The filtered solid was dissolved in pyridine and heated, cooled to normal temperature, and then filtered. Recrystallization from chloroform and ethyl acetate gave chemical formula 1A.

After the above compound 1A (8.96 g,21.8 mmol) and 2, 4-diphenyl-6- (3 '- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) - [1,1' -biphenyl ] -3-yl) -1,3, 5-triazine (11.15 g,21.8 mmol) were completely dissolved in tetrahydrofuran (100 ml), potassium carbonate (9 g,65.4 mmol) was dissolved in 50ml of water and added thereto, tetrakis (triphenylphosphine) palladium (756 mg,0.65 mmol) was added thereto, and the mixture was heated and stirred for 8 hours. After the reaction was completed by lowering the temperature to normal temperature, the potassium carbonate solution was removed and the white solid was filtered. The white solid obtained by filtration was washed with tetrahydrofuran and ethyl acetate, respectively, 2 times, whereby the above-mentioned compound 1-1 (12 g, yield 77%) was produced.

In the synthesis method of the compound 1-1, if the reactant is changed, other compounds represented by chemical formula 1 may be synthesized.

For example, in the synthesis of compound 1A, if naphthalene-1-ol is used instead of 4-bromophenol, a core shown by compound 1B described below can be synthesized.

In addition, in the synthesis of compound 1A, if the position where the bromo group is substituted is changed, the position on the nucleus where the substituent is substituted may be changed.

However, the method of synthesizing the compound represented by chemical formula 1 is not limited to the above method, and other methods may be used.

< Synthesis of Compound of chemical formula 2 >

The method of synthesizing the compound represented by chemical formula 2 according to an embodiment of the present invention will be described by taking the synthesis examples of the compounds 2-2 and 2-3 as examples.

[ Synthesis of Compound 2-2 ]

Compound 4A (26 g,35.4 mmol), compound 4B (9.31 g,35.4 mmol) and potassium carbonate (K) ₂ CO ₃ ) (14.7 g,106 mmol) in Tetrahydrofuran (THF) (500 mL), H ₂ O (150 ml) was heated to 90 ℃. Tetrakis (triphenylphosphine) palladium (Pd (PPh) ₃ ) ₄ ) (0.8 g,0.71 mmol) was followed by refluxing for 4 hours. After cooling to room temperature, the aqueous layer was removed. Magnesium sulfate (MgSO) was added to the organic layer ₄ ) And then filtering. After concentration, purification was performed by column chromatography to give Compound 2-2 (18 g, yield 78) ％)。

[ Synthesis of Compound 2-3 ]

Compound 3A (15 g,34.8 mmol), compound 3B (18.63 g,69.6 mmol) and potassium carbonate (K) ₂ CO ₃ ) (28.7 g,208 mmol) in Tetrahydrofuran (THF) (500 mL), H ₂ O (150 ml) was heated to 90 ℃. Tetrakis (triphenylphosphine) palladium (Pd (PPh) ₃ ) ₄ ) (1.6 g,1.4 mmol) was followed by refluxing for 12 hours. After cooling to room temperature, the aqueous layer was removed. Magnesium sulfate (MgSO) was added to the organic layer ₄ ) And then filtering. After concentration, purification was performed by column chromatography, whereby compound 2-3 (15 g, yield 67%) was obtained.

In the above synthetic methods of the compounds 2-2 and 2-3, if the reactants are changed, other compounds represented by chemical formula 2 may be synthesized. However, the synthetic method of chemical formula 2 is not limited to the above method, and other methods may be used.

< examples 1 to 1>

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) in a film having a thickness of 100nm was put into distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent was a product of fei-hill co., and the distilled water was filtered 2 times by a Filter (Filter) manufactured by millbore co., ltd. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.

On the ITO transparent electrode thus prepared, hexanitrile hexaazatriphenylene (HAT-CN; hexanitrile hexaazatriphenylene) was subjected to thermal vacuum evaporation at a thickness of 50nm to form a hole injection layer. On the hole injection layer, the compound HT1 was vacuum-evaporated to a thickness of 40nm to form a hole transport layer. On the hole transport layer, a host compound BH1 and a dopant compound BD1 were vacuum-evaporated at a weight ratio of 97.5:2.5, thereby forming a light-emitting layer having a thickness of 30 nm. On the light-emitting layer, a hole blocking layer (electron control layer) having a thickness of 5nm was formed by vapor deposition of compound 1-1, and an electron injection and transport layer having a thickness of 35nm was formed by vacuum vapor deposition of compound 2-1 and LiQ (8-hydroxyquinoline lithium, lithium Quinolate) at a weight ratio of 1:1. On the electron injection and transport layer, lithium fluoride (LiF) was evaporated to a thickness of 1.2nm and aluminum was evaporated to a thickness of 200nm in this order to form a cathode. Thereby manufacturing an organic light emitting device.

In the above process, the vapor deposition rate of the organic matter is maintained at 0.04nm/sec to 0.07nm/sec, the vapor deposition rate of lithium fluoride is maintained at 0.03nm/sec, the vapor deposition rate of aluminum is maintained at 0.2nm/sec, and the vacuum degree is maintained at 2×10 during vapor deposition ^-7 To 5X 10 ^-6 The support is thus fabricated into an organic light emitting device.

< examples 1-2 to 13-6>

An organic light-emitting device was fabricated by the same method as in example 1-1, except that the compounds of table 1 below were used instead of the compounds 1-1 and 2-1.

/>

Comparative example 1 ]

An organic light emitting device was fabricated by the same method as the above-described example 1-1, except that the electron injection and transport layer was not formed.

Comparative example 2 ]

An organic light emitting device was fabricated by the same method as the above-described example 1-1, except that a hole blocking layer was not formed.

Comparative example 3 ]

An organic light-emitting device was fabricated in the same manner as in example 1-1, except that compound 2-1 was used instead of compound 1-1 in the hole blocking layer, and compound 1-1 was used instead of compound 2-1 in the electron injection and transport layer.

Comparative example 4 ]

An organic light-emitting device was fabricated in the same manner as in example 1-1, except that compound 1-3 was used instead of compound 1-1 in the hole blocking layer, and compound NPD was used instead of compound 2-1 in the electron injection and transport layer.

At 10mA/cm ² The luminous efficiency of the organic light-emitting device manufactured in the above experimental example was measured at a current density of 20mA/cm ² The time required for 98% relative to the initial brightness was measured (LT 98). The results are shown in table 1 below.

[ Table 1 ]

/>

From table 1, it was confirmed that the driving voltage of the organic light emitting device including the first organic layer including the compound of chemical formula 1 and the second organic layer including the compound of chemical formula 2 was reduced, and the efficiency, particularly, the lifetime characteristics were significantly improved.

Claims

1. An organic light emitting device, comprising:

a cathode;

an anode provided opposite to the cathode;

a light-emitting layer provided between the cathode and the anode;

a first organic layer that is provided between the cathode and the light-emitting layer and that contains a compound represented by chemical formula 1; and

a second organic layer that is provided between the cathode and the first organic layer and that contains a compound represented by the following chemical formula 2:

chemical formula 1

In the chemical formula 1 described above, a compound having the formula,

x is O or S, and the X is O or S,

at least one of R1 to R16 is a group represented by the following chemical formula A, and the others are the same as or different from each other, and each is independently hydrogen, alkyl, or aryl substituted or unsubstituted with alkyl, or is combined with each other with an adjacent group to form an aromatic hydrocarbon ring,

Chemical formula A

In the chemical formula a, in which the amino acid is represented by the formula a,

at least one of X1 to X3 is N, the rest are CR,

r is hydrogen or is together with- (L2) _l2 Ar2 or- (L3) _l3 Ar3 is bonded to form an aromatic hydrocarbon ring substituted or unsubstituted with a heterocyclic group,

ar2 and Ar3 are the same as or different from each other and are each independently an aryl group substituted or unsubstituted with an alkyl group, a haloalkyl group, a haloalkoxy group, or a heteroaryl group; silyl groups substituted or unsubstituted with alkyl groups or aryl groups; or a heterocyclic group substituted or unsubstituted with an alkyl group, or an aryl group,

l1 to l3 are each independently an integer of 1 to 3,

when L1 is 2 or more, 2 or more L1 s are the same or different from each other,

when L2 is 2 or more, 2 or more L2 s are the same or different from each other,

when L3 is 2 or more, 2 or more L3 s are the same or different from each other,

represents a binding site to the chemical formula 1,

chemical formula 2

In the chemical formula 2 described above, the chemical formula,

at least one of Y1 to Y3 is N, and the remainder are CH,

g1 and G2 are the same or different from each other and are each independently an aryl group substituted or unsubstituted with an aryl group,

l11 and L12 are the same or different from each other and are each independently a substituted or unsubstituted aromatic hydrocarbon ring group of 2 to 4 valences or a substituted or unsubstituted heterocyclic group of 2 to 4 valences,

a to d are each independently an integer of 1 to 3, and

when a to d are 2 or more, structures in parentheses of 2 or more are the same or different from each other.

2. The organic light-emitting device according to claim 1, wherein the first organic layer is a hole blocking layer, the second organic layer is an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the hole blocking layer is provided in contact with the light-emitting layer.

3. The organic light-emitting device according to claim 1, wherein the compound represented by the chemical formula 1 and the compound represented by the chemical formula 2 satisfy the following formula 1:

1 (1)

|P _El |＞|P _Eb |

In the above-mentioned formula (1),

|P _Eb i represents an absolute value of a dipole moment of the compound represented by the chemical formula 1,

|P _El I represents the absolute value of the dipole moment of the compound represented by the chemical formula 2.

4. The organic light emitting device of claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1 or 1-2:

chemical formula 1-1

Chemical formula 1-2

In the chemical formulas 1-1 and 1-2,

l1 to L3, L1 to L3, ar2, ar3 and X1 to X3 are as defined in the formula A,

at least one of X4 to X6 is N, and the others are CR',

r' is hydrogen, or is together with- (L5) _l5 Ar4 or- (L6) _l6 Ar5 is bonded to form an aromatic hydrocarbon ring substituted or unsubstituted with a heterocyclic group,

ar4 and Ar5 are the same as or different from each other and are each independently an aryl group substituted or unsubstituted with an alkyl group, a haloalkyl group, a haloalkoxy group, or a heteroaryl group; silyl groups substituted or unsubstituted with alkyl groups or aryl groups; or a heterocyclic group substituted or unsubstituted with an alkyl group, or an aryl group,

l4 to l6 are each independently an integer of 1 to 3,

when L4 is 2 or more, 2 or more L4 s are the same or different from each other,

when L5 is 2 or more, 2 or more L5 s are the same or different from each other,

when L6 is 2 or more, 2 or more L6 s are the same or different from each other,

n1 is an integer of 0 to 2,

n2 is an integer of 0 to 2,

1≤n1+n2≤4，

r100 and r101 are each independently integers from 1 to 8,

1≤r100+n1≤8，

1≤r101+n2≤8，

when R100 is 2 or more, 2 or more R100 are the same or different from each other, and

5. The organic light-emitting device according to claim 1, wherein the chemical formula 2 is represented by any one of the following chemical formulas 2-1 to 2-3:

chemical formula 2-1

Chemical formula 2-2

Chemical formula 2-3

In the chemical formulas 2-1 to 2-3,

y1 to Y3, G1, G2, L11, L12, G11, b and d are as defined in said chemical formula 2,

at least one of Y4 to Y6 is N, and the remainder are CH,

at least one of Y7 to Y9 is N, and the others are CH, and

G3 to G6 are the same or different from each other and are each independently aryl substituted or unsubstituted aryl.

6. The organic light-emitting device according to claim 1, wherein the compound represented by chemical formula 1 is selected from the following compounds:

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7. the organic light-emitting device according to claim 1, wherein the compound represented by chemical formula 2 is selected from the following compounds:

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8. an organic light-emitting device according to claim 1 wherein the light-emitting layer comprises a host and a dopant and the dopant has a maximum emission wavelength in the range 420nm to 520 nm.

9. The organic light-emitting device according to claim 8, wherein the host comprises at least one of compounds represented by the following chemical formulas 3-1 and 3-2:

chemical formula 3-1

Chemical formula 3-2

In the chemical formulas 3-1 and 3-2,

l31 to L35 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

ar31 to Ar35 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

r200 is an integer of 1 to 8,

r201 is an integer of 1 to 7,

when R200 is 2 or more, 2 or more R200 are the same or different from each other, and

10. The organic light-emitting device of claim 8, wherein the host is any one or more selected from the group consisting of:

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11. the organic light-emitting device of claim 1, wherein the organic light-emitting device comprises 2 or more light-emitting layers.

12. The organic light-emitting device according to claim 11, wherein maximum emission wavelengths of at least 2 layers of the 2 or more light-emitting layers are different from each other.

13. The organic light-emitting device of claim 11, wherein at least one of the 2 or more light-emitting layers comprises a phosphorescent dopant, and

at least one layer comprises a fluorescent dopant.

14. The organic light-emitting device of claim 1, wherein the organic light-emitting device comprises: a first light-emitting layer provided between the anode and the first organic layer; and

a second light-emitting layer provided on the first light-emitting layer.

15. The organic light-emitting device of claim 1, wherein the organic light-emitting device comprises: a first light-emitting layer provided with a part between the anode and the first organic layer; and

And a second light-emitting layer provided between the anode and the first organic layer.

16. The organic light-emitting device of claim 1, wherein the organic light-emitting device comprises: a first light-emitting layer provided between the anode and the first organic layer;

a second light-emitting layer provided on the first light-emitting layer, and

and a third light-emitting layer provided on the second light-emitting layer.